Fight 3: The Surgeon Somehow, he drugs Connor just before the fight itself. Just remember to Break Defense and use Counter-throws against the barrels on the side of the ring to create openings for yourself. While he does not get a sword he is decently tough. Fight 2: The Docker Once again, 3 associates need to be dealt with first. It does not take too much after that to finish him off though. He will gain the sword once into the red for health. Just focus on this, even after he is given his sword. There are barrels in a few spots, these are great for when you need to plant someone's face into something. A few universal notes: The crowd will attack Connor if he gets to close to the edge, keep some distance. Now it is time to get through the Tournament itself. Once there just head under the fence and it will not be too long for you to find the rest. You need to head to the Old Brewery in Boston. The Tournament Now it is time for the Brawling Tournament itself. Once again use Counter-throw or Break Defense (for once) to get through his guard and take him down. Once again, talk with him to start the fight then it is onto taking out his associates. You will find him inside a Windmill yard. The Merchant This Brawler is found in New York in the Northeast. There is a work bench nearby where you first encounter him. To take him down you need to throw him into barrels and tables until his health bar is depleted. He is only susceptible to Counter-throws. Immediately take down his associates so you can focus on the Rope Beater. He is, of course, marked with the Boston Brawlers icon. The Rope Beater He is found in the Ropeyard near the docks in Eastern Boston. He, like the others can break your melee combo so be wary of it. He is susceptible to Counter-disarms so use that to create the opening Connor needs to pummel him. Once again, start with his associates then focus in on the Stinger. He is marked with the Boston Brawlers icon. The Stinger This Brawlers is found out in the Frontier in the Diamond Basin to the East of the lake inside the region. Take down the associates then focus on the second smuggler. A second smuggler and 2 associates appear for you to fight. Once you get him down to below half health he calls out for some help. Once again, you need to use Counter-disarm and Counter-Throw to break his defense. He starts with 3 associates to take down and then you can work him over a little. The Smuggler The Smuggler is found in the Northern part of Central Boston, once again marked with a Boston Brawlers icon. Use this to create the opening you need to start and finish him with a good pummeling. He is susceptible to the Counter-disarm though. The sailor will block normal attacks and is immune to the Counter-kill. Use Counter-kills to take out his friends then you move onto the sailor himself. You will find him on his ship with 3 friends. The Sailor Head to New York and go for the next Boston Brawler marker in the Western part of New York. He will push you away during some of your chains so be ready for it.
To get through to Bunyon himself use the Counter-disarm or throw to create an opening and follow it up with numerous attacks. Bunyon himself cannot be taken down with a Counter-kill, however his associates are quite susceptible to that. From there talk with him to start the fight itself. He is in a stable yard with 3 associates.
Assassin's Creed 3 – Club Challenges: The Boston Brawlers – Missions Peter Bunyon He is found in the Frontier in Troy's Wood Region, marked with the Boston Brawler icon on the main map.